On Tuesday, August 21st, gunmen stop a Chicago & West Michigan Passenger Trail from Chicago. Ties were placed across the track, but the train was not running fast enough to be derailed by them before Engineer George Zibbel stopped the train. Five men had drawn revolvers and two bullets were sent through the window of the cab, shattering the glass, while Engineer George Zibbel dropped to his knees.

The brakeman and Conductor Rice were ordered to stay on the train at gun point. Locked alone in the express car, expressman Bernard VanOtten was ordered to open up. As VanOtten did not open the door, one of the robbers shattered the door with a stick of dynamite. Two of the robbers went in blowing the doors off the safe. Unfortunate for the robbers, the safe was empty. The other bandits proceeded to the passenger car and held up Conductor E.E. Rice, shoving a revolver under his nose, taking 88 dollars from him. The other crooks took Engineer Zibbel and the fireman's watches. After several miscellaneous shots were fired, doing no damage, the robbers ran into the woods.

Sheriff Stratton was notified by C. & W. M. officials, while Sheriff Whitbeck and Detective Johnson shadowed the tracks of the two men to Allegan where they were caught by local officers. Detective Brewster of Grand Rapids, Superintendent Smith of Detroit and Manager Wormley of the American Express Company continued the investigation.

A day later, after the hold up, Edward Daggett a local farmer, found a horse hitched in his barn that he thought had to do with the burglary since the horses worn shoes indicate it was from the city.

A night before the hold up, Wentworth's hardware store in Benton Harbor was broken into and seven revolvers were taken.

A day after the robbery, two men answering the description of the Fennville robbers boarded the Lake Shore train in Dorr and rode to Eagle Mills. The two men were found after boarding a Grand Rapids & Indiana train heading north. When Police Detective George W. Powers boarded the train and attempted to arrest the men, the gunmen both drew revolvers and lodged a bullet in Power's brain. Later, detective Powers died in Butterworth hospital while the robbers escaped.